Principles of Acid-Base Alkaloid

Extractions in relation to N,N-

Dimethyltryptamine

1st Edition

By:

Bodhisativa

Psilosopher

Medicine Man
 TABLE OF CONTENTS

1. INTRODUCTION
2. CHEMISTRY 101
1. THE THEORY OF ACID-BASE REACTIONS
2. THE THEORY OF PH
3. MOLARITY
4. WHAT IS POLARITY?
5. SO WHAT DOES THIS HAVE TO DO WITH DMT?
3. EXTRACTION METHOGOLOY
4. AFTERWORD
5. REFERENCES
 1. Introduction:

Purpose for this guide

This guide is designed for novices who aren’t familiar with chemistry. There are many novices who are
very interested in DMT, but often get caught up in the scientific jargon. This, hopefully, will resolve that.
This guide is NOT designed for novices who take shortcuts and are impatient to try the spice. This is
written with the intention that every reader will thoroughly read and reread in order to fully understand
the theory of acid-base extractions.

The secondary purpose for this guide is to provide a basic framework to conduct comparative assays on
various plant material for comparison of active alkaloid levels.

Which procedure should I use?

There are 2 main extraction techniques utilised in the extraction of DMT. The acid-to-base extraction
(ATB) and the straight-to-base (STB) extraction. Both of these techniques rely on the precipitation of
freebase DMT within a solvent. However, in order to obtain freebase DMT, it must be extracted from the
plant material. DMT is soluble in acids, and so ATB is widely used. ATB is preferable to STB for only
one circumstance; the species of plant material used. Typically, ATB is preferred when using fat laden
plant species, such as Acacias. The DMT is located in the central vacuole of the plant cell, so in chemical
processing, we try to break apart all the plant structures. This is the reason for acid simmering steps that
last several hours. However, when you break apart the entire structure, it is inevitable that you will extract
some unwanted compounds, most common being fats and oils. These are harmless, but lower the purity of
the final product. In DMT extractions, we try to extract alkaloids only, and leaving behind all the plant
fats and oils. It is impossible to know the constituents of your product by the naked eye, but all successful
extractions have similar properties. In order to fully analyse your handiwork, it is recommended to run a
thin-layer chromatography (TLC) on the sample. The DMT Nexus has recently organised TLC kits for the
purpose of extraction analyses, which can be bought on the link below:

http://www.lunarlaboratories.com/

It is not necessary to analyse the product if it looks similar to other extracts, but it’s a technique that you
have at your disposal should you wish to pursue an active interest in the extraction techniques of plant-
based entheogens.

STB is typically used for not-so-fat-laden species, such as Mimosa hostilis. The procedure is exactly the
same as ATB, without the acid.
 2. Chemistry 101:

2.1 The theory of acid-base reactions

It would be career suicide for a chemistry lecturer to talk about acids and bases without mentioning
Brønsted and Lowry. Brønsted and Lowry were two chemists who independently defined what an acid
and a base is. But before we go into the Brønsted-Lowry definition, it’s better to understand the history of
defining acids and bases. So first, we’ll discuss the Arrhenius definition. Svante Arrhenius was a Swedish
chemist, who in the 1880’s described an acid as “A substance that produces H+ ions in aqueous solution”,
and a base as “A substance that produces OH- in aqueous solution”.

A practical explanation of this is HCl(g). Notice the subscript with a “g”? That means the compound is in a
gaseous state. HCl(aq) is hydrochloric acid and HCl(g) is hydrogen chloride. In gaseous form HCl, is a
covalent compound, i.e. it is not bound to anything else except itself. Once it enters the aqueous phase by
being dissolved in water, it forms ionic bonds with water molecules. Therefore, hydrochloric acid is an
ionic solution. However, when we say that “it” forms ionic bonds with water, we refer to the H+ ion only.
Cl- does not play a part in acids or bases.

H+ binds to water to form an ionic compound called a hydronium ion. The chemical equation looks like
this:

H+ + H2O  H3O+

Chemists often use H+ and H3O+ interchangeably. They both denote the same thing, which is an H+ that
has been dissolved in water.
A little factoid here; an H+ ion is just a proton. A hydrogen atom consists of 1 proton in the nucleus and 1
electron spinning around it. Once the atom loses the electron and becomes H+, it is left with only a proton.

So with this in mind, we’ll now move on to the currently accepted definition of acids and bases, as
proposed by Brønsted and Lowry. The Arrhenius definition isn’t wrong, per se, it’s just that the Brønsted-
Lowry definition is more correct, if that makes sense.

The Brønsted-Lowry definition is focused on the transfer of H+ ions rather than producing them. Since a
H+ ion is a proton, Brønsted-Lowry defined an acid and base as this:

Acid: A proton donor

Base: A proton acceptor

You may ask, “how are the two definitions different?” For the purposes of DMT extraction, both are
correct. But for advanced chemistry, the Arrhenius definition becomes a bit confusing, mainly because
ammonia (NH3) acts as a base. We won’t go into that, but if you’re interested, check out the acid-base
section of any chemistry textbook.
So, what happens in an acid-base extraction? The best way to explain this is through a chemical equation.

The general rule is: acid + base  salt + water

So if we use hydrochloric acid and sodium hydroxide, the equation is this:

HCl(aq) + NaOH(aq)  NaCl(aq) + H2O

So the products of this reaction are sodium chloride (table salt) and water. This only happens when equal
concentrations of HCl and NaOH are mixed. If the HCl is in excess, for example, all of the NaOH will be
consumed to make NaCl(aq), but there will still be some HCl in the solution. Therefore, the solution will
still be acidic, albeit not as acidic.

So now we move on to determining concentrations of solutions.

2.2 The theory of pH

So now we’ve established what an acid is, but haven’t fully gone into what a base is. I’ve left it for this
section since it is useful for explaining pH as well. It is also here that we will see why the Arrhenius
definition doesn’t hold up to the Brønsted-Lowry definition.

pH stands for “potential hydrogen”. On the pH scale, 7 is neutral. Lower than 7 is acidic, higher than 7 is
basic or alkaline.

The calculation of pH is:

pH = -log[H3O+]

The square brackets denote concentration. This will be covered in the Molarity section.

The pH scale is a logarithmic scale.

An increase of 1 on the pH scale corresponds to a decrease in the concentration of H3O+ by a factor of 10.
 2.3 Molarity
Molarity is the concentration of a solution. If we say 2M HCl, that means the HCl has a concentration of 2
moles per litre. So, what is a mole? It is a small furry animal that likes to dig. It is also an SI unit of
measurement that indicates amount of a substance. Moles are dependent on two things, the mass of the
substance, and the molecular mass of the substance. What’s molecular mass? To understand this, we need
to break down the Periodic Table of Elements.

Let’s zoom in to the first element, hydrogen.

The atomic number is used to order all the elements according to their atomic size. The symbol and name
is self-explanatory. What we’re interested in is the atomic mass. Atomic mass is the same as molecular
mass, which is also the same as molar mass. It is the mass of one mole of that element, in grams. So 1
mole of lithium is 6.941 grams.

Here is the calculation for number of moles:

Number of moles = Mass (in grams) / molecular mass

So if you have 3 grams of lithium, the calculation is:

Number of moles = 3 / 6.941

= 0.43 mol

To calculate molarity, the formula is:

Number of moles = concentration x volume (in litres)

OR

Concentration = number of moles / volume (in litres)

So let’s use a real life example pertaining to DMT to sum this all up. We want to make a 2M solution of
NaOH.

First thing is to weigh out 2 moles of NaOH. Using the Periodic Table, 1 mole of NaOH is:

22.99 (molar mass of Na) + 15.99 (molar mass of O) + 1.008 (molar mass of H) = 39.99 g.

Since we want 2 moles, we double this amount. So 79.98 g. We then prepare 500ml of COLD distilled
water. We slowly dissolve all of the NaOH into the water. Once it is fully dissolved, we check the volume
again. It should be more than 500ml. We then bring up the volume to 1L with fresh distilled water (which
does not mean add another 500ml). And there we go, we have just made a 2M NaOH solution.

It is important not to just add all of the NaOH into 1L of water. Just because it will dissolve doesn’t mean
it won’t occupy space. If you added all of the NaOH into 1L of water, the final volume will be much
higher than 1L.

2.4 What is polarity?

Polarity refers to the overall charge of the molecule. Polar means it is slightly charged, non-polar means it
is not charged at all.

Water has an overall positive charge, it is polar. The charges on methane cancel out, so it is non-polar.
Oxygen is diatomic, and only has one kind of atom, so it is non-polar.

This is essentially all there is to polarity in relation to extractions. The golden rule of polarity is:

Like dissolves like

Polar things will dissolve in other polar things. Non-polar things will dissolve in other non-polar things.
Polar things will NOT dissolve in non-polar things. Non-polar things will NOT dissolve in polar things. I
know, very scientific to use the word “things”.
 2.5 So what does this have to do with DMT?

When DMT is dissolved in hydrochloric acid (HCl), it forms DMT hydrochloride, when it is dissolved in
acetic acid (CH3COOH), it forms DMT acetate. From here, the acid can then be neutralised with a base.
In chemical terms:

acid + base  salt + water

So hydrochloric acid and sodium hydroxide (NaOH) will look like this:

HCl(aq) + NaOH(aq)  NaCl(aq) + H2O

(If you recall, the subscript denotes the state the compound is in. Aq means aqueous. HCl is actually a gas
and only becomes an acid when it is dissolved in water). NaCl is table salt. Once the acid has been
neutralised, which includes the DMT hydrochloride, the DMT has nowhere else to go, and is floating
around in the solution in freebase form. From here, a solvent is added to allow the DMT to migrate to a
liquid that has a much lower freezing point than what conventional freezers can produce. This allows for
the use of conventional household freezers to freeze precipitate the DMT within the solvent. This has 2
advantages over precipitation by evaporation. Firstly, it takes a much shorter amount of time. The time for
a freeze precipitation is in the span of a day or two, but evaporation will take a few days to a few weeks to
fully evaporate, depending on your climate. The second advantage is that you will be keeping the solvent.
The solvent can be washed and used ad infinitum. Having to buy new solvent for every extract will end up
costing a lot, if you have many failures or conduct many extracts.
 3. Extraction Methodology

MATERIALS:

1) 100g of your plant material of choice. ACRB (Acacia confuse root bark) powder was used here.
2) Magnetic hotplate stirrer and stir bar
3) A strong magnet (to remove the stir bar)
4) Pyrex glass water bath
5) 1 x 1000ml Erlenmeyer flask
6) 1x ≥ 1000ml beaker
7) 500 mL measuring cylinder
8) 50 mL turkey baster
9) 1.0 ml eyedropper
10) Plastic funnel
11) Glass thermometer
12) 0.001M HCl stock solution (see first step in this section on how to prepare stock solution)
13) 5M NaOH stock solution (see first step in this section on how to prepare stock solution)
14) Naphtha or any non-polar solvent.
15) 80g of non-iodised NaCl (table salt).
16) Rectangular Pyrex dish (preferably with an airtight and watertight locking lid)
17) Razor blade

METHOD:

Preparing stock solution:

NOTE: The HCl and NaOH were acquired from a hardware store. According to their packaging, the HCl
states “Contains min. 320g/L of hydrochloric acid solution”. For NaOH, the packaging states “Contains:
98% Sodium hydroxide.”

1) Acquire 2 large and fairly sturdy HDPE containers. Distilled water containers found at hardware
stores are suitable, but something a bit sturdier would be preferred. Pick a size appropriate for
you. Recommended minimum is 5L capacity.
2) Thoroughly wash the containers. This is not necessary if the container was for distilled water. It is
ideal to use the distilled water to make the stock solution in the first place.
3) Calculate the amounts required to get achieve desired concentration.

FOR HCl:

Assuming the concentration is 320g/L. A pH of 2-4 is ideal. For arguments sake, we will calculate a pH
of 3. To achieve this pH we will use the following formula.

pH = -log[H3O+]
As can be seen on the scale in the pH section, the concentration is 10-3. This is equates to 0.001M HCl,
which is why this particular concentration is specified in the Materials section. Now, we need to calculate
the concentration of the undiluted HCl.

First, we calculate the number of moles:

Number of moles = Mass (in grams) / molecular mass

= 320 / 36.458 (atomic weight of H and Cl)

= 8.777…

Therefore, the number of moles in 1L is 8.777. Which means the molarity is 8.78M (rounded to 2
significant figures).

Now, we figure out how much we need to dilute the concentrated HCl solution.

Let’s say we want 10L of final stock solution.

We use the following formula (which we haven’t covered before):

C1V1 = C2V2

1 refers to the concentrated solution. 2 refers to the diluted solution. C is concentration and V is volume.
For volume, it’s best to use mL.

So we have the following information: C1 = 8.77, C2 = 0.001, V2 = 10000 (10L). We want V1, which will
tell us the volume of concentrated HCl to add into 10L of water.

8.77 x V1 = 0.001 x 10000

V1 = (0.001 x 10000) / 8.77

= 1.14 mL

Therefore, we add 1.14 mL into 10L of water. If you want to be ultra-scientific, you would add 1.14 mL
of acid into 9.99886 L of water, since the concentrated solution is contributing to the overall volume. For
our purposes, this isn’t necessary.

FOR NaOH:

Since NaOH is in a solid state, we will measure out the amount of NaOH needed. First we need to
calculate the mass of 1 mole of NaOH.

1 mole of NaOH is:

22.99 (molar mass of Na) + 15.99 (molar mass of O) + 1.008 (molar mass of H) = 39.99 g.

We want 5 M, so we multiply this mass by 5, which gives us 199.95 grams per litre of water.
Preparing NaOH stock solution is a bit different to HCl, due to safety concerns. Pouring the NaOH
granules into water will create an exothermic reaction, i.e. it releases heat. A LOT of it. So we cannot
prepare the entire 10L in one go.

We must create the solution 1 litre at a time.

1) Prepare 500ml of COLD distilled water in a 1L borosilicate Erlenmeyer flask.

2) Slowly dissolve all of the NaOH into the water. It is advisable to add a small amount, and swirl
the solution around to dissolve it. Then add more and swirl it again. Repeat until all NaOH is
dissolved in solution. This will prevent a rapid increase in temperature.
3) Bring up the volume to 1L with fresh distilled water (which does not mean add another 500ml).
An Erlenmeyer flask is not known for its accuracy in measuring volume, but for our intents and
purposes, it will suffice.
4) Leave the flask to cool down. Pouring hot NaOH solution into a HDPE container may damage the
container, so it’s best to err on the safe side.
5) Repeat steps 1-4 up till the desired volume is achieved.

This is a tedious process, but it is necessary.

It is not required to be ultra-precise with preparing any solution for a DMT extract, but is recommended.

Acid-base extraction:

1) Place Pyrex glass water bath on magnetic hotplate stirrer.

2) Pour 600mL of 0.001M HCl stock solution into a 1000mL Erlenmeyer flask.
3) Drop the stir bar into the Erlenmeyer flask, by tilting the flask and allowing the stir bar to roll
down the side. Do not drop it straight in.
4) Place Erlenmeyer flask in water bath. Fill the water bath with warm water until it is level with the
solution in the flask.
5) Turn the heat and stir function on. Do not set either too high. Stir bar should be swirling the
solution gently. The ideal temperature for the acid solution in this extraction is 60°C.
6) Slowly add 100g of ACRB powder into the flask using the plastic funnel. Try to prevent the
powder from touching the sides of the flask. NOTE: It is likely that the stir bar will cease to spin
when adding either too much powder or adding it too quick. In the event this happens, occasional
manual swirling is required.
7) Leave the flask in the water bath for a minimum of 2 hours. If the stir bar ceases to spin, it is
advisable to remove it now using the strong magnet. Simply place the magnet on the outside
surface of the flask. Move the magnet around if it is not attracting the stir bar. Once it is attracted,
drag the magnet along the surface of the flask and bring it up to the mouth of the flask. Once it is
near the mouth, place the flask on a flat surface and use a gloved hand or tweezers to pick up the
stir bar. Moving the magnet too rapidly can cause the stir bar to fall back down into the solution.
This may cause damage to your flask. Finesse is key here.
8) After 2 hours, add 80g of non-iodised NaCl (table salt)
9) Slowly pour 200mL of 5M NaOH stock solution into the flask. The solution should go black.
Turn the heat down a little bit. Ideal temperature is 50-60°C.
10) Leave the flask in the water bath for at least 1 hour. A longer wait time can be beneficial. Swirl
occasionally if the stir bar ceases to move or was removed in step 7.
11) Remove stir bar if it hasn’t been removed already.
12) Add 80mL of naphtha or your non-polar solvent into the flask.
13) Pour entire contents of flask into the ≥ 1000ml beaker. Pour back and forth between the flask and
beaker. This will thoroughly mix the 2 layers. The more you mix the layers, the more surface of
the solvent will be exposed to the freebase DMT. Alternatively, if you have an alkali-resistant
stopper, you can use it on the flask and shake. Do not shake too vigourously. There will be
pressure buildup. Remember to remove the stopper after shaking to prevent pressure buildup.
14) Pour all the solution into the flask and let it sit in the water bath for 10 minutes or until both
layers are clearly formed.
15) Careful decant this solution from the flask into the 500mL measuring cylinder. Since the non-
polar solvent layer is on top, the majority of it will be poured into the cylinder. NOTE: Do not
pour all of the solution in; the cylinder cannot hold it all. Pour as much as the cylinder can hold,
giving some leeway to prevent spills.
16) Using a turkey baster, carefully pipette the top non-polar solvent into a rectangular Pyrex dish.
Use two hands to keep the turkey baster steady, and pipette by touching the tip of the turkey
baster to the side of the cylinder, just below the surface of the non-polar solvent. Stop when
you’re getting too close to the basified layer.
17) Using the 1.0mL eyedropper, the remainder of the non-polar solvent can be pipetted. You can rest
the palm of your pipetting hand against the side of the cylinder to keep it steady. Your other hand
should hold the cylinder to prevent it from falling. The tip of the eyedropper should be resting
against the inner surface of the cylinder and just under the surface of the solvent layer.
18) Repeat steps 12-17 thrice.
19) Place the rectangular Pyrex dish with the solvent into the freezer. Make sure the lid is locked in.
If your dish does not come with a locking lid, then wrap the opening of the dish with cling film
and place the entire dish into a large zip lock bag. Zip it up, and place in the freezer.
Alternatively, you can let it evaporate completely in a dry place. If evaporating, skip to step 22.
20) Leave the dish in the freezer for a minimum of 24 hours. Do not disturb the dish before 24 hours
are up, the crystals may not form properly otherwise.
21) After 24 hours, carefully decant the solvent down the drain. It is recommended that you keep the
solvent in another glass container for long term storage. This used solvent can be used ad
infinitum.
22) Scrape up the precipitate with a razor blade, and place on a small section of baking paper. This
can be wrapped up, and stored in a cool, dark and dry place.
 4. Afterword

So there you have it. You have successfully extracted N,N-Dimethyltryptamine. What you do with this
sacred molecule is up to you. “With great power comes great responsibility” - Voltaire.

I would like to give thanks to all the people on the DMT-Nexus who have provided valuable information
and support in regards to everything DMT related, and life in general.

A special thanks go out to cyb, chemisTryptaMan and Earthwalker who provided the basic structure of
this methodology. All I did was tweak their work. This would not be possible without them.

Bodhisativa, Psilosopher and Medicine Man may or may not be the same person suffering from a severe
case of identity dissolution.

5. References
cyb, chemisTryptaMan (2013). The cyb/CTM ‘Maximum Yield’ ATB Salt tek MAX ION. Wherever the
hell cyb and CTM are from: DMT-Nexus

Earthwalker (2014). ACRB TEK 100g "PICS" (Newbie Friendly). Wherever the hell EW is from: DMT-
Nexus

Tro, N. (2011). Chemistry. 2nd ed. Upper Saddle River, New Jersey: Pearson.

Various pictures taken from this textbook and stolen from Google Image searches. Sorry.

2016

Published exclusively on The DMT Nexus.